Two years ago, I made the leap to go from working weddings on the side to working weddings full-time. I haven’t looked back since and I have never once regretted my decision to pursue this full-time. One of my most frequently asked questions from colleagues is if I have tips for someone looking to make the same jump from side hustle to working full time, while balancing a day job.

Rebecca Chan Weddings and Events
Unfortunately I don’t always wake up looking like this and I don’t play with flowers for a living.. but I still enjoy my work! Photo: Jessilynn Wong Photography

For some, it seems like the dream life to quit the rat race and pursue your passion, but there are a lot of real questions that need to be answered before it can be reality. Some people start from nothing and it works for them. But as a planner (naturally), I’ve got some tips to consider that I personally thought through before I made the leap.

Here were my tips before calling it quits:

Count your costs.

Do you have a budget? I’m not talking about wedding budgets. I’m talking about your personal monthly expenses.

If you don’t, you should start one.

What are your monthly and annual household expenses that you manage?
Do you have debts to pay off?
Do you have an emergency fund?

As a practical numbers person, I recommend you to count the costs and check numbers so you know where you are at. At the very least, a starting goal will be to cover your own personal expenses if you want to work for yourself. Leading me to my next point.

Set goals.

With my husband being a fairly risk-adverse personality, I had  to have a monetary monthly number as my goal for it to even remotely make sense to consider wedding planning full time.

I knew that I wanted to at least duplicate the income I was bringing in from my day job to pay my bills, so I had an a monthly amount that was my goal. Weddings are a cyclical industry, with half your cash flow coming from initial deposits and half from final payments.

You will need to figure out what your monthly cash flow is with your existing bookings, and project for the following year, to get an estimate for the cash flow you will have for the calendar year.

Keep in mind when you work weddings full time, you will have 40 more hours in the week to dedicate to sales and getting more work, so expect your capacity to take on clients to increase.

Buy a house first.

Easier said than done in Toronto’s crazy housing market! Banks and mortgage agents don’t generally favour new business owners. If owning a house is important to you, you may want to get that done first with your day job income on paper.

Otherwise if you work for yourself only, mortgage lenders will determine your eligibility for a mortgage based on the average of the last two years of business based on your last two tax returns.

It’s common for businesses to not make a lot of money on paper the first few years, especially if you are doing it on the side (Did you only bring in $10,000 of gross revenue on your tax return last year? Well, that’s going to be used for determining your eligibility for a mortgage!).

Fun fact: The day after I bought my house and closed, I quit my day job 😀

Have you done enough weddings to see the good, the bad and the ugly?

Weddings are not all fuzzy wuzzy and full of pretty things. Wedding days, yes, are pretty and can be enjoyable experiences.

But have you had bad clients yet?
Have you successfully worked with clients in a full planning capacity?

Practically speaking, you want to have a very real taste of what wedding planning would be like in all its glory (good and bad), before you make the leap to pursue it full-time.

Just do it.

Beyond the practical tips and careful planning, at some point you just need to commit to the idea to go full time and just do it (assuming financially you are prepared, you have family support and you have some business brewing). Just like most challenges that are bold/scary/unchartered, the biggest step is just to get started.

If you are thinking about making the leap, all the best to you! For me, it was one of the best decisions I have ever made and I do not regret it one second. But it did take a little bit of planning to ensure I did it right.


Rebecca Chan is a Toronto wedding planner and day of wedding coordinator providing sophisticated planning for the style-savvy couple. Whether you need planning assistance or wedding day coordination, Rebecca can help you create your dream wedding day. Contact her today, she'd love to hear from you.

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